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Chianti to Montalcino, the Birthplace of Brunello

Few things in this world live up to the hype. But everything you've ever heard about Tuscany is true. It's not a destination. It's a sublime experience. Routes lined with cypress trees overlooking the patchwork vineyards below will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see; imagine the wines, flavors and luxuries you'll discover.

Itinerary

Day
1The quintessential Tuscan journey, offering the most scenic routes from Florence to Montalcino Sample fresh Tuscan specialties at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields Pedal to medieval Greve in Chianti, where you can stroll through the narrow lanes and pretty piazza of this former market town before continuing to the splendid Castello del Nero Kick off the week with superb Michelin-starred cuisine inspired by Tuscan traditions and flavors.

Days
2-3Ascend quiet roads into the heart of the Chianti region Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore Visit Badia a Coltibuono (Abbey of the Good Harvest), where you're treated to a private tour and olive oil tasting Wine and dine in style at San Felice's renowned restaurant.

Day
4Visit Monte Oliveto Maggiore, a Benedictine abbey featuring some of the best preserved frescoes in Europe Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings Stroll Montalcino's medieval streets in search of the perfect trattoria for dinner.

Days
5-6The narrow streets of Montalcino, known for harboring the region's finest wines, are yours to discover Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills Taste world-famous Brunello Pedal through the undulating wheat fields and hilltop towns of the Val d'Orcia In Pienza, marvel at extraordinary Renaissance architecture and sample splendid pecorino cheese Visit the imposing abbey of Sant'Antimo, where monks celebrate mass with stirring Gregorian chants.

Call 800-462-2848, Every day 6am-6pm,PST

Premiere Inns

Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking
on your desired date on the Dates & Prices tab.

Castello del Nero

Tavarnelle Val di Pesa (1 night) A castle with a Michelin-starred restaurant steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)

Borgo San Felice

San Felice (2 nights) Described by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)

Castello di Velona

Castelnuovo dell'Abate (2 nights) Soak up superb hilltop views at this elegant 11th-century fortress featuring a magnificent vantage point above the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)

Guest Reviews About This Trip

Beyond special...the indulgence of a consistent 5-star experience in locations only experienced in the movies.

Fredric Levin- Aspen, CO

We had a spectacular trip. I made the comment to my wife after the very first day of biking that I could go home today and feel like all my expectations had been fulfilled - and that was just the first day! Thanks, Backroads, for the trip of a lifetime!

Michael Kellum- Allen, TX

We had a fabulous time - our leaders were fantastic!! We loved the fact that support was always available and that we periodically saw the other group members on the road but for much of the time it was just the two of us enjoying the scenery and the ride. We can't wait to come back and do another Backroads trip. Meals were fantastic and we totally enjoyed the flexibility to ride as much or as little as we wanted. All in all it was definitely the best vacation ever - can't wait to download my 500+ pictures - everywhere was "una bella vista."

This Trip Is Rated Level 2-5

Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.

Daily Route Options

Day

EASYGOING

ACTIVE

AVID

Level 1

Level 2

Level 3

Level 4

Level 5

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

1

19

1300

2

24*

1800

40*

2200

48

3100

3

19*

1800

29

2400

36

3100

46

3900

4

28*

1200

33*

1200

48

2700

5

22*

2000

32*

2400

45

3500

62

4400

6

14

900

note:

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.